40. Xu P, Huang L (2017) Effects of α-cypermethrin enantiomers on the growth, biochemical
parameters and bioaccumulation in Rana nigromaculata tadpoles of the anuran amphibians.
Ecotoxicol Environ Saf 139:431–438. https://doi.org/10.1016/j.ecoenv.2017.02.015
41. Jin Y, Wang J, Sun X et al (2013) Exposure of maternal mice to cis-bifenthrin
enantioselectively disrupts the transcription of genes related to testosterone synthesis in male
offspring. Reprod Toxicol 42:156–163. https://doi.org/10.1016/j.reprotox.2013.08.006
42. Hu F, Li L, Wang C, Zhang Q, Zhang X, Zhao M (2010) Enantioselective induction of
oxidative stress by permethrin in rat adrenal pheochromocytoma (PC12) cells. Environ
Toxicol Chem 29:683–690. https://doi.org/10.1002/etc.73
43. Katagi T (2012) Environmental behavior of synthetic pyrethroids. In: Matsuo N, Mori T (eds)
Pyrethroids. Topics in current chemistry. Springer, Berlin
44. Ye J, Zhao M, Liu J, Liu W (2010) Enantioselectivity in environmental risk assessment of
modern chiral pesticides. Environ Pollut 158:2371–2383. https://doi.org/10.1016/j.envpol.
2010.03.014
45. Li ZY, Zhang ZC, Zhang L, Leng L (2008) Stereo and enantioselective degradation of
β-cypermethrin and β-cyfluthrin in soil. Bull Environ Contam Toxicol 80:335–339. https://
doi.org/10.1007/s00128-008-9368-y
46. Yao G, Jing X, Peng W et al (2015) Chiral insecticide α-cypermethrin and its metabolites:
stereoselective degradation behavior in soils and the toxicity to earthworm Eisenia fetida.
J Agric Food Chem 63:7714–7720. https://doi.org/10.1021/acs.jafc.5b03148
47. Qin S, Budd R, Bondarenko S, Liu W, Gan J (2006) Enantioselective degradation and chiral
stability of pyrethroids in soil and sediment. J Agric Food Chem 54:5040–5045. https://doi.
org/10.1007/s00128-007-9099-5
48. Zhang C, Liu X, Jiang W et al (2018) Enantioselective degradation of the chiral alphacypermethrin and detection of its metabolites in five plants. Environ Sci Pollut Res
26:1558–1564. https://doi.org/10.1007/s11356-018-3594-6
49. Li S, Li Z, Li Q, Zhao J, Li S (2016) Characterization of diastereo- and enantioselectivity in
degradation of synthetic pyrethroids in soils. Chirality 28:72–77. https://doi.org/10.1002/chir.
22544
50. Qin S, Gan J (2006) Enantiomeric differences in permethrin degradation pathways in soil and
sediment. J Agric Food Chem 54:9145–9151. https://doi.org/10.1021/jf061426l
51. Zhang P, Yu Q, He Y, Zhu W, Zhou Z, He L (2017) Chiral pyrethroid insecticide
fenpropathrin and its metabolite: enantiomeric separation and pharmacokinetic degradation
in soils by reverse-phase high-performance liquid chromatography. Anal Methods 9:4439.
https://doi.org/10.1039/c7ay01124e
52. Birolli WG, Arai MS, Nitschke M, Porto ALM (2019) The pyrethroid (Æ)-lambda-cyhalothrin
enantioselective biodegradation by a bacterial consortium. Pestic Biochem Physiol. https://doi.
org/10.1016/j.pestbp.2019.02.014
53. Mullin LS, Sheets LP, Clark JM et al (2002) Mechanisms of pyrethroid neurotoxicity:
implications for cumulative risk assessment. Toxicology 171:3–59. https://doi.org/10.1016/
s0300-483x(01)00569-8
54. Ali MA, Baugh PJ (2003) Sorption-desorption studies of six pyrethroids and mirex on soils
using GC/MS-NICI. Int J Environ Anal Chem 83:923–933. https://doi.org/10.1080/
03067310310001608759
55. Zhang B, Zhang H, Jin B, Tang L, Yang J, Li B, Zhuang G, Bai Z (2008) Effect of
cypermethrin insecticide on the microbial community in cucumber phyllosphere. J Environ
Sci 20:1356–1362
56. Cycon M, Piotrowska-Seget Z (2016) Pyrethroid-degrading microorganisms and their potential for the bioremediation of contaminated soils: a review. Front Microbiol 7:1–26. https://doi.
org/10.3389/fmicb.2016.01463
57. Alves PRL, Cardoso EJBN (2016) Overview of the standard methods for soil ecotoxicology
testing. In: Invertebrates – experimental models in toxicity screening. InTech, Rijeka,
pp 35–56
172
C. E. T. Parente et al.
parameters and bioaccumulation in Rana nigromaculata tadpoles of the anuran amphibians.
Ecotoxicol Environ Saf 139:431–438. https://doi.org/10.1016/j.ecoenv.2017.02.015
41. Jin Y, Wang J, Sun X et al (2013) Exposure of maternal mice to cis-bifenthrin
enantioselectively disrupts the transcription of genes related to testosterone synthesis in male
offspring. Reprod Toxicol 42:156–163. https://doi.org/10.1016/j.reprotox.2013.08.006
42. Hu F, Li L, Wang C, Zhang Q, Zhang X, Zhao M (2010) Enantioselective induction of
oxidative stress by permethrin in rat adrenal pheochromocytoma (PC12) cells. Environ
Toxicol Chem 29:683–690. https://doi.org/10.1002/etc.73
43. Katagi T (2012) Environmental behavior of synthetic pyrethroids. In: Matsuo N, Mori T (eds)
Pyrethroids. Topics in current chemistry. Springer, Berlin
44. Ye J, Zhao M, Liu J, Liu W (2010) Enantioselectivity in environmental risk assessment of
modern chiral pesticides. Environ Pollut 158:2371–2383. https://doi.org/10.1016/j.envpol.
2010.03.014
45. Li ZY, Zhang ZC, Zhang L, Leng L (2008) Stereo and enantioselective degradation of
β-cypermethrin and β-cyfluthrin in soil. Bull Environ Contam Toxicol 80:335–339. https://
doi.org/10.1007/s00128-008-9368-y
46. Yao G, Jing X, Peng W et al (2015) Chiral insecticide α-cypermethrin and its metabolites:
stereoselective degradation behavior in soils and the toxicity to earthworm Eisenia fetida.
J Agric Food Chem 63:7714–7720. https://doi.org/10.1021/acs.jafc.5b03148
47. Qin S, Budd R, Bondarenko S, Liu W, Gan J (2006) Enantioselective degradation and chiral
stability of pyrethroids in soil and sediment. J Agric Food Chem 54:5040–5045. https://doi.
org/10.1007/s00128-007-9099-5
48. Zhang C, Liu X, Jiang W et al (2018) Enantioselective degradation of the chiral alphacypermethrin and detection of its metabolites in five plants. Environ Sci Pollut Res
26:1558–1564. https://doi.org/10.1007/s11356-018-3594-6
49. Li S, Li Z, Li Q, Zhao J, Li S (2016) Characterization of diastereo- and enantioselectivity in
degradation of synthetic pyrethroids in soils. Chirality 28:72–77. https://doi.org/10.1002/chir.
22544
50. Qin S, Gan J (2006) Enantiomeric differences in permethrin degradation pathways in soil and
sediment. J Agric Food Chem 54:9145–9151. https://doi.org/10.1021/jf061426l
51. Zhang P, Yu Q, He Y, Zhu W, Zhou Z, He L (2017) Chiral pyrethroid insecticide
fenpropathrin and its metabolite: enantiomeric separation and pharmacokinetic degradation
in soils by reverse-phase high-performance liquid chromatography. Anal Methods 9:4439.
https://doi.org/10.1039/c7ay01124e
52. Birolli WG, Arai MS, Nitschke M, Porto ALM (2019) The pyrethroid (Æ)-lambda-cyhalothrin
enantioselective biodegradation by a bacterial consortium. Pestic Biochem Physiol. https://doi.
org/10.1016/j.pestbp.2019.02.014
53. Mullin LS, Sheets LP, Clark JM et al (2002) Mechanisms of pyrethroid neurotoxicity:
implications for cumulative risk assessment. Toxicology 171:3–59. https://doi.org/10.1016/
s0300-483x(01)00569-8
54. Ali MA, Baugh PJ (2003) Sorption-desorption studies of six pyrethroids and mirex on soils
using GC/MS-NICI. Int J Environ Anal Chem 83:923–933. https://doi.org/10.1080/
03067310310001608759
55. Zhang B, Zhang H, Jin B, Tang L, Yang J, Li B, Zhuang G, Bai Z (2008) Effect of
cypermethrin insecticide on the microbial community in cucumber phyllosphere. J Environ
Sci 20:1356–1362
56. Cycon M, Piotrowska-Seget Z (2016) Pyrethroid-degrading microorganisms and their potential for the bioremediation of contaminated soils: a review. Front Microbiol 7:1–26. https://doi.
org/10.3389/fmicb.2016.01463
57. Alves PRL, Cardoso EJBN (2016) Overview of the standard methods for soil ecotoxicology
testing. In: Invertebrates – experimental models in toxicity screening. InTech, Rijeka,
pp 35–56
172
C. E. T. Parente et al.